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Windstar Cruise Deals

Expert Deal
The Price you found is a great deal, 80% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $71/night to be a bargain.
$999*
14 nights
Transatlantic Cruise Deal
Wind Surf
|
Inside Cabin
Departing
Apr 09, 2019
From St. Maarten
  • Day 1
    St. Maarten
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Ponta Delgada
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Lisbon

Wind Surf - Windstar Cruises

Pros

Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

Cons

No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

Bottom Line

Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

Expert Deal
The Price you found is a great deal, 80% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $71/night to be a bargain.
$999*
14 nights
Transatlantic Cruise Deal
Wind Surf
|
Outside Cabin
Departing
Apr 09, 2019
From St. Maarten
  • Day 1
    St. Maarten
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Ponta Delgada
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Lisbon

Wind Surf - Windstar Cruises

Pros

Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

Cons

No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

Bottom Line

Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

Expert Deal
The Price you found is a great deal, 79% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $75/night to be a bargain.
$1,199*
16 nights
Alaska Cruise Deal
Star Legend
|
Suite
Departing
May 06, 2019
From Yokohama
  • Day 1
    Yokohama
  • Day 2
    Cruising
  • Day 3
    Miyako Island
  • Day 4
    Hakodate
  • Day 5
    Aormori
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Dutch Harbor
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Kodiak
  • Day 16
    Homer
  • Day 17
    Seward

Star Legend - Windstar Cruises

Pros

Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

Cons

Without sails, it lacks some of the panache of Windstar's original iconic ships

Bottom Line

Ideal for active couples seeking a romantic, small ship atmosphere

Expert Deal
The Price you found is a great deal, 79% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $75/night to be a bargain.
$1,199*
16 nights
Alaska Cruise Deal
Star Legend
|
Outside Cabin
Departing
May 06, 2019
From Yokohama
  • Day 1
    Yokohama
  • Day 2
    Cruising
  • Day 3
    Miyako Island
  • Day 4
    Hakodate
  • Day 5
    Aormori
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Dutch Harbor
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Kodiak
  • Day 16
    Homer
  • Day 17
    Seward

Star Legend - Windstar Cruises

Pros

Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

Cons

Without sails, it lacks some of the panache of Windstar's original iconic ships

Bottom Line

Ideal for active couples seeking a romantic, small ship atmosphere

Expert Deal
The Price you found is a great deal, 77% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $80/night to be a bargain.
$1,199*
15 nights
Transatlantic Cruise Deal
Wind Star
|
Outside Cabin
Departing
Mar 30, 2019
From Barbados
  • Day 1
    Barbados
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Lisbon

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 77% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $80/night to be a bargain.
$1,199*
15 nights
Transatlantic Cruise Deal
Wind Star
|
Inside Cabin
Departing
Mar 30, 2019
From Barbados
  • Day 1
    Barbados
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Lisbon

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 76% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $85/night to be a bargain.
$1,099*
13 nights
Transatlantic Cruise Deal
Star Pride
|
Outside Cabin
Departing
Mar 19, 2019
From San Juan
  • Day 1
    San Juan
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Horta
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Lisbon

Star Pride - Windstar Cruises

Pros

Service-driven, laid-back luxury, with longer visits in lesser-known ports of call

Cons

Lacks big ship bells and whistles

Bottom Line

Great for active couples looking for romance on a sophisticated ship

Expert Deal
The Price you found is a great deal, 76% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $85/night to be a bargain.
$1,099*
13 nights
Transatlantic Cruise Deal
Star Pride
|
Inside Cabin
Departing
Mar 19, 2019
From San Juan
  • Day 1
    San Juan
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Horta
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Lisbon

Star Pride - Windstar Cruises

Pros

Service-driven, laid-back luxury, with longer visits in lesser-known ports of call

Cons

Lacks big ship bells and whistles

Bottom Line

Great for active couples looking for romance on a sophisticated ship

Expert Deal
The Price you found is a great deal, 76% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $85/night to be a bargain.
$1,099*
13 nights
Transatlantic Cruise Deal
Star Pride
|
Suite
Departing
Mar 19, 2019
From San Juan
  • Day 1
    San Juan
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Horta
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Lisbon

Star Pride - Windstar Cruises

Pros

Service-driven, laid-back luxury, with longer visits in lesser-known ports of call

Cons

Lacks big ship bells and whistles

Bottom Line

Great for active couples looking for romance on a sophisticated ship

Expert Deal
The Price you found is a great deal, 74% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $92/night to be a bargain.
$1,099*
12 nights
Transatlantic Cruise Deal
Star Breeze
|
Outside Cabin
Departing
Apr 14, 2019
From Barbados
  • Day 1
    Barbados
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Lisbon

Star Breeze - Windstar Cruises

Pros

Small-ship cruising, port-intensive itineraries

Cons

Limited entertainment and enrichment activities

Bottom Line

Terrific upscale yet casual cruise line for active travelers

Expert Deal
The Price you found is a great deal, 74% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $92/night to be a bargain.
$1,099*
12 nights
Transatlantic Cruise Deal
Star Breeze
|
Inside Cabin
Departing
Apr 14, 2019
From Barbados
  • Day 1
    Barbados
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Lisbon

Star Breeze - Windstar Cruises

Pros

Small-ship cruising, port-intensive itineraries

Cons

Limited entertainment and enrichment activities

Bottom Line

Terrific upscale yet casual cruise line for active travelers

Expert Deal
The Price you found is a great deal, 74% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $92/night to be a bargain.
$1,099*
12 nights
Transatlantic Cruise Deal
Star Breeze
|
Suite
Departing
Apr 14, 2019
From Barbados
  • Day 1
    Barbados
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Lisbon

Star Breeze - Windstar Cruises

Pros

Small-ship cruising, port-intensive itineraries

Cons

Limited entertainment and enrichment activities

Bottom Line

Terrific upscale yet casual cruise line for active travelers

Expert Deal
The Price you found is a great deal, 73% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $94/night to be a bargain.
$1,499*
16 nights
Alaska Cruise Deal
Star Legend
|
Balcony
Departing
May 06, 2019
From Yokohama
  • Day 1
    Yokohama
  • Day 2
    Cruising
  • Day 3
    Miyako Island
  • Day 4
    Hakodate
  • Day 5
    Aormori
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Dutch Harbor
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Kodiak
  • Day 16
    Homer
  • Day 17
    Seward

Star Legend - Windstar Cruises

Pros

Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

Cons

Without sails, it lacks some of the panache of Windstar's original iconic ships

Bottom Line

Ideal for active couples seeking a romantic, small ship atmosphere

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,399*
14 nights
Transatlantic Cruise Deal
Wind Surf
|
Inside Cabin
Departing
Nov 30, 2019
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Antigua
  • Day 15
    St. Maarten

Wind Surf - Windstar Cruises

Pros

Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

Cons

No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

Bottom Line

Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,399*
14 nights
Transatlantic Cruise Deal
Wind Star
|
Inside Cabin
Departing
Nov 12, 2019
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    St. Maarten

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,399*
14 nights
Transatlantic Cruise Deal
Wind Star
|
Outside Cabin
Departing
Nov 12, 2019
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    St. Maarten

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,399*
14 nights
Transatlantic Cruise Deal
Wind Surf
|
Outside Cabin
Departing
Nov 30, 2019
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Antigua
  • Day 15
    St. Maarten

Wind Surf - Windstar Cruises

Pros

Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

Cons

No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

Bottom Line

Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

Expert Deal
The Price you found is a great deal, 67% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $115/night to be a bargain.
$1,499*
13 nights
Transatlantic Cruise Deal
Star Pride
|
Balcony
Departing
Mar 19, 2019
From San Juan
  • Day 1
    San Juan
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Horta
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Lisbon

Star Pride - Windstar Cruises

Pros

Service-driven, laid-back luxury, with longer visits in lesser-known ports of call

Cons

Lacks big ship bells and whistles

Bottom Line

Great for active couples looking for romance on a sophisticated ship

Expert Deal
The Price you found is a great deal, 61% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $136/night to be a bargain.
$1,499*
11 nights
Eastern Caribbean Cruise Deal
Wind Star
|
Inside Cabin
Departing
Mar 12, 2019
From Puntarenas (Puerto Caldera)
  • Day 1
    Puntarenas (Puerto Caldera)
  • Day 2
    Quepos
  • Day 3
    Puerto Jimenez
  • Day 4
    Isla Parida
  • Day 5
    Cruising
  • Day 6
    Contadora Isle
  • Day 7
    Panama Canal (Cruising)
  • Day 8
    Colon (Cristobal)
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Aruba

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 61% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $136/night to be a bargain.
$1,499*
11 nights
Eastern Caribbean Cruise Deal
Wind Star
|
Outside Cabin
Departing
Mar 12, 2019
From Puntarenas (Puerto Caldera)
  • Day 1
    Puntarenas (Puerto Caldera)
  • Day 2
    Quepos
  • Day 3
    Puerto Jimenez
  • Day 4
    Isla Parida
  • Day 5
    Cruising
  • Day 6
    Contadora Isle
  • Day 7
    Panama Canal (Cruising)
  • Day 8
    Colon (Cristobal)
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Aruba

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.